Lease Renewal with Increase and Other Requests

[Polina Goncharova]

Hello BP!

I own a 3 Flat property on Chicago's Near West Side and I am planning on increasing rent in the following manner:

(Rent increase is due to market rents and a hike in property tax)

3bd/2ba, 1,150 sq ft Apartment

Current $1,150

Market $1,500+

Renewal $1,350

I am being gentle as I prefer to receive $1,500 but flipping the unit could cost more due cleaning and repaint costs (20+ft ceiling). But would like to ask if it is within reason to make maintenance requests with this renewal. The tenant has caused some damage to walls and I would request they either put a deposit of $300 or fix the damage on their own. Is that reasonable to request although I was not the original landlord that rented the unit to him? I don't have documentation on who caused the damage and there is no deposit. 

Do you have suggestions on ways that I could protect the integrity of the property while being reasonable and firm with a $200 rent increase?

Thank you all so much,

Polina